C-allyl salicylic acid.



D g1 ATES 13 ATENT OFFICE.

LUIDWIG CLAISEN, or connsnnnc, NEAR BONN, GERMANY, ASSIGNOR 'ro SYNTHETIC rnrnnrs 00., me, on NEW YORK, N. Y., A CORPORATION OF NEW Yomc -c,-ALI.'YLTsA IcYLIc ACID.

1,994,123. No Drawing.

To all whom it may concern:

Be it known that I, LUDWIG CLAISEN, doctor of philosophy, professor of chemistry,-

' citizen of the German Empire; residing at Godesberg, near 'Bonn-omthe-Rhine, Germany, have invented new and useful Im proveinents in C-Allyl Salicylic Acid, of which the following is a specification.

I have found that the hitherto unknown C-ortho-allyl-salicylic acid being a- Valuableantipyretic having most probably the formula:

can be obtained by heating the O-allylsalicylic-acid-ester and saponifying the resulting C-allylsalicylic-acid-ester. The reaction proceeds in accordance with the following equation: I

cocoon. I coon C-allylsalicylic O-nll lsalicylicy acid ester.

' C-allylsalicylic acid. acid-ester.

The new C-allylsalicylic acid crystallizes from dilute methyl alcohol in the shape of colorless needles melting at 96 C. Its

aqueous or alcoholic solution is colored violet by a ferric chlorid solution.

In order to illustrate my new process the following example is given, thepartsbeing O-allylsalicylic-acld-ethyl-ester,

by weight sem no. 798,055. I

which is'a colorless oil boiling at 153 C. under a pressure of 13 mm., is heated in an oil bath during onehour to 230 C.. and "the resulting-mass is distilled. The C-allylsalicylic-acid-ethyl-ester passes over at 270278' C. It boils in vacuo (12 mm.) at 142 Itsalcoholic solution iscolored blue-violet with ferric chlorid. For the saponifica'tion the ester is heated during half an hour with.

the equal quantity by weight of a per cnt'solution of KOH in alcohol and the resulting oil is extracted with a mixture of ether with chloroform.

I claim v The new C-allyl-salicylic acid having most probably the formula:

crystallizing' from dilute methyl alcohol in the-shape of needles melting at 96 0.; its

alcoholic solution being colored violet with ferric chlorid; forming esters with alcohols; and being a-valuable antipyretic, sub,- stantially as described; I

I In testimony whereof I have hereunto set my-hand in the presencelof two subscribing witnesses.

- I LUDWIGCLAISEN.

-Witnesses: EDwA nFERTLc,

HANS Bm'ic'KNER. 

